TWI751230B - High vertical dielectric liquid crystal composition and liquid crystal display element - Google Patents
High vertical dielectric liquid crystal composition and liquid crystal display element Download PDFInfo
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- TWI751230B TWI751230B TW106141191A TW106141191A TWI751230B TW I751230 B TWI751230 B TW I751230B TW 106141191 A TW106141191 A TW 106141191A TW 106141191 A TW106141191 A TW 106141191A TW I751230 B TWI751230 B TW I751230B
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- 0 *C(CC1)CCC1C(CC1)CCC1c1ccc(-c(cc2F)cc(F)c2F)c(F)c1 Chemical compound *C(CC1)CCC1C(CC1)CCC1c1ccc(-c(cc2F)cc(F)c2F)c(F)c1 0.000 description 9
- UEMGWPRHOOEKTA-UHFFFAOYSA-N Fc1cc(F)ccc1 Chemical compound Fc1cc(F)ccc1 UEMGWPRHOOEKTA-UHFFFAOYSA-N 0.000 description 1
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Abstract
本發明公開了包含有一種液晶組合物,包含有一種或多種式I所示化合物、一種或多種式II所示化合物以及一種或多種式III所示化合物,
Description
本發明屬於液晶材料技術領域,具體涉及一種高垂直介電液晶組合物及其含有此類液晶的液晶顯示元件。 The invention belongs to the technical field of liquid crystal materials, and in particular relates to a high vertical dielectric liquid crystal composition and a liquid crystal display element containing such liquid crystals.
目前,液晶化合物的應用範圍拓展的越來越廣,其可應用於多種類型的顯示器、光電元件、感測器等中。用於上述顯示領域的液晶化合物的種類繁多,其中向列相液晶應用最為廣泛。向列相液晶已經應用在被動TN、STN矩陣顯示器和具有TFT主動矩陣的系統中。 At present, the application range of liquid crystal compounds is expanding more and more widely, and it can be applied to various types of displays, optoelectronic components, sensors, and the like. There are many kinds of liquid crystal compounds used in the above-mentioned display field, among which nematic liquid crystal is the most widely used. Nematic liquid crystals have been used in passive TN, STN matrix displays and systems with TFT active matrices.
對於薄膜晶體管技術(TFT-LCD)應用領域,近年來市場雖然已經非常巨大,技術也逐漸成熟,但人們對顯示技術的要求也在不斷的提高,尤其是在實現快速響應,降低驅動電壓以降低功耗等方面。液晶材料作為液晶顯示器重要的光電子材料之一,對改善液晶顯示器的性能發揮重要的作用。 For the application field of thin film transistor technology (TFT-LCD), although the market has been very large and the technology has gradually matured in recent years, people's requirements for display technology are also constantly improving, especially in the realization of fast response, reducing the driving voltage to reduce power consumption, etc. As one of the important optoelectronic materials of liquid crystal display, liquid crystal material plays an important role in improving the performance of liquid crystal display.
作為液晶材料,需要具有良好的化學和熱穩定性以及對電場和電磁輻射的穩定性。而作為薄膜晶體管技術(TFT-LCD)用液晶材料,不僅需要具有如上穩定性外,還應具有較寬的向列相溫度範圍、合適的雙折射率各向異性、非常高的電阻率、良好的抗紫外線性能、高電荷保持率以及低蒸汽壓等性能。 As a liquid crystal material, it is required to have good chemical and thermal stability and stability to electric fields and electromagnetic radiation. As a liquid crystal material for thin film transistor technology (TFT-LCD), it not only needs to have the above stability, but also has a wide nematic temperature range, suitable birefringence anisotropy, very high resistivity, good UV resistance, high charge retention and low vapor pressure.
對於動態畫面顯示應用,消除顯示畫面殘影和拖尾,要求液晶具有很快的響應速度,因此要求液晶具有較低的旋轉黏度γ1。另外,對於可攜式設 備,為了降低設備能耗,希望液晶的驅動電壓盡可能低。而對於電視等用途的顯示器來說,對於液晶的驅動電壓要求不是那麼的低。 For the application of dynamic image display, to eliminate the afterimage and tailing of the display image, the liquid crystal is required to have a fast response speed, so the liquid crystal is required to have a low rotational viscosity γ1. In addition, for portable devices In order to reduce the power consumption of the device, it is hoped that the driving voltage of the liquid crystal is as low as possible. For displays such as televisions, the driving voltage requirements for liquid crystals are not so low.
液晶化合物的黏度,尤其是旋轉黏度γ1直接影響液晶加電後的響應時間,不管是上升時間(ton)還是下降時間(toff),都與液晶的旋轉黏度γ1成正比關係,上升時間(ton)由於與液晶盒和驅動電壓有關,可以藉由加大驅動電壓的方法與降低液晶盒盒厚來調節。而下降時間(toff)與驅動電壓無關,主要是與液晶的彈性常數與液晶盒盒厚有關,盒厚的趨薄會降低下降時間(toff),而不同顯示模式下,液晶分子的運動方式不一樣,TN、IPS、VA三種模式分別與平均彈性常數K、扭曲彈性常數、彎曲彈性常數成反比關係。 The viscosity of the liquid crystal compound, especially the rotational viscosity γ1, directly affects the response time of the liquid crystal after power-on. Whether it is the rise time (t on ) or the fall time (t off ), it is proportional to the rotational viscosity γ1 of the liquid crystal, and the rise time ( t on ) is related to the liquid crystal cell and the driving voltage, and can be adjusted by increasing the driving voltage and reducing the thickness of the liquid crystal cell. The fall time (t off ) has nothing to do with the driving voltage, but is mainly related to the elastic constant of the liquid crystal and the cell thickness of the liquid crystal cell. The thinning of the cell thickness will reduce the fall time (t off ), and under different display modes, the movement of the liquid crystal molecules The methods are different. The three modes of TN, IPS, and VA are inversely proportional to the average elastic constant K, torsional elastic constant, and bending elastic constant, respectively.
依照液晶連續體理論,各種不同的液晶在外力(電場、磁場)作用下發生形變後,會藉由分子間的相互作用,會“回彈”回原來的形狀。同樣地,液晶也是由於分子間的相互作用力形成“黏度”。液晶分子的微小變化,會使液晶的常規參數性能發生明顯的變化,這些變化有的是有一定規律的,有的似乎不易找到規律,對於液晶分子間的相互作用也會產生明顯的影響,這些影響非常微妙,至今也沒有形成很完善的理論解釋。 According to the liquid crystal continuum theory, after various liquid crystals are deformed under the action of external force (electric field, magnetic field), they will "rebound" back to their original shape through the interaction between molecules. Similarly, liquid crystals form "viscosity" due to intermolecular interactions. Small changes in liquid crystal molecules will cause significant changes in the conventional parameters and performance of liquid crystals. Some of these changes have certain rules, and some of these changes seem to be difficult to find. They will also have a significant impact on the interaction between liquid crystal molecules. These effects are very important. Subtle, so far there is no perfect theoretical explanation.
液晶的黏度與液晶分子結構有關,研究不同液晶分子形成的液晶體系的黏度與液晶分子結構之間的關係是液晶配方工程師的重要任務之一。 The viscosity of liquid crystal is related to the molecular structure of liquid crystal. It is one of the important tasks of liquid crystal formulation engineers to study the relationship between the viscosity of liquid crystal system formed by different liquid crystal molecules and the molecular structure of liquid crystal.
液晶面板能耗高的原因是只有大約5%左右的背光能夠穿透顯示元件,而被人眼捕獲,絕大部分光是被“浪費”了的。如果能夠開發出光穿透率高的液晶,即能夠降低背光強度,從而實現節省能耗的目的,延長設備的使用時間。 The reason for the high energy consumption of LCD panels is that only about 5% of the backlight can penetrate the display elements, and most of the light is "wasted" when captured by the human eye. If a liquid crystal with high light transmittance can be developed, the intensity of the backlight can be reduced, thereby achieving the purpose of saving energy and prolonging the use time of the device.
本發明需要解決的技術問題是提供一種液晶組合物具有良好的對光和熱的穩定性,較低的黏度,可以藉由調節單體比例得到較為寬泛的折射率、較高的清晰點(很寬的使用溫度範圍),尤其是液晶組合物具有較高的光的穿透率,因而顯示元件具有較高的亮度或是具有節能省電的效果。 The technical problem to be solved by the present invention is to provide a liquid crystal composition with good stability to light and heat, low viscosity, and a relatively broad refractive index and a high sharpness point (very high clarity) can be obtained by adjusting the monomer ratio. Wide use temperature range), especially the liquid crystal composition has higher light transmittance, so the display element has higher brightness or has the effect of energy saving.
為了解決以上技術問題,本發明提供了一種液晶組合物,包含有一種或多種式I所示化合物、一種或多種式II所示化合物以及一種或多種式III所示化合物:
其中,R1、R2、R3、R5、R6各自獨立地表示碳原子數為1-10的烷基、碳原子數為1-10的烷氧基、碳原子數為2-10的鏈烯基或碳原子數為3-8的鏈烯氧基,且R1、R3所示基團中任意一個或多個不相連的CH2可以被環戊基、環丁基、環丙基、-O-替代;R4表示F、CF3、OCF3、OCHF2或OCH2F; 、各自獨立地表示、、、、、 或任意氟代苯中的一種或多種; 、各自獨立地表示苯或氟代苯中的一種或兩種; 表示、、或任意氟代苯中的一種或多種; m、p、w各自獨立地表示1、2或3; n、q各自獨立地表示0或1。 wherein R 1 , R 2 , R 3 , R 5 , and R 6 each independently represent an alkyl group having 1-10 carbon atoms, an alkoxy group having 1-10 carbon atoms, or an alkyl group having 2-10 carbon atoms. alkenyl group or alkenyloxy group with 3-8 carbon atoms, and any one or more unconnected CH 2 in the groups represented by R 1 and R 3 can be replaced by cyclopentyl, cyclobutyl, cyclopentyl Propyl, -O- substitution; R 4 represents F, CF 3 , OCF 3 , OCHF 2 or OCH 2 F; , represent independently , , , , , or one or more of any fluorobenzene; , Each independently represents one or both of benzene or fluorobenzene; Express , , Or one or more of any fluorobenzene; m, p, w each independently represent 1, 2 or 3; n, q each independently represent 0 or 1.
所述一種或多種式I所示化合物較佳為式I1至I14所示化合物中的一種或多種化合物;所述一種或多種式II所示化合物較佳為式II1至II14所示化合物中的一種或多種化合物;所述一種或多種式III所示化合物較佳為式III1至III5所示化合物中的一種或多種化合物,
其中,R11、R31各自獨立地表示碳原子數為1-6的烷基;R21各自獨立地表示碳原子數為1-5的烷基;R51、R61各自獨立地表示碳原子數為1-6的烷基、碳原子數為1-6的烷氧基、碳原子數為2-6的鏈烯基或碳原子數為3-6的鏈烯氧基。 Wherein, R 11 and R 31 each independently represent an alkyl group having 1-6 carbon atoms; R 21 each independently represent an alkyl group having 1-5 carbon atoms; R 51 and R 61 each independently represent a carbon atom An alkyl group having 1-6 carbon atoms, an alkoxy group having 1-6 carbon atoms, an alkenyl group having 2-6 carbon atoms, or an alkenyloxy group having 3-6 carbon atoms.
本發明所述液晶組合物中,該一種或多種式I所示化合物總質量百分比含量較佳為1-40%,該一種或多種式II所示化合物總質量百分比含量較佳為1-40%,該一種或多種式III所示化合物總質量百分比含量較佳為1-80%。 In the liquid crystal composition of the present invention, the total mass percentage content of the one or more compounds represented by formula I is preferably 1-40%, and the total mass percentage content of the one or more compounds represented by formula II is preferably 1-40% , the total mass percentage content of the one or more compounds represented by formula III is preferably 1-80%.
式I所示化合物同時具有較大的液晶分子長軸平行方向、垂直方向的介電各向異性,而長軸平行方向、垂直方向的介電各向異性差值(△ε)較小。式II所示化合物同時具有較大的液晶分子長軸平行方向、垂直方向的介電 各向異性,長軸平行方向、垂直方向的介電各向異性差值(△ε)較大。兩者結合使用,具有明顯的提升混合液晶的垂直方向的介電各向異性的作用,而不會使混合液晶的△ε變小,因此添加量不會受到△ε的限制,可以實現較大量的添加,從而大幅度提升液晶混合物的穿透率。式III化合物具有低的旋轉黏度,進一步具有較高的清晰點(CP),與式I和式II所示化合物一起組合使用,液晶混合物的旋轉黏度很低,響應速度快。 The compound represented by formula I also has relatively large dielectric anisotropy in the direction parallel to the long axis and the vertical direction of the liquid crystal molecules, while the difference (Δε) in the dielectric anisotropy in the direction parallel to the long axis and the vertical direction is small. The compound represented by the formula II has a large dielectric in the parallel direction and the vertical direction of the long axis of the liquid crystal molecule at the same time. Anisotropy, the difference (Δε) of dielectric anisotropy between the long axis parallel direction and the vertical direction is large. The combination of the two can obviously improve the dielectric anisotropy of the mixed liquid crystal in the vertical direction without making the Δε of the mixed liquid crystal smaller, so the addition amount will not be limited by Δε, and a larger amount can be achieved. The addition of , thereby greatly improving the transmittance of the liquid crystal mixture. The compound of formula III has low rotational viscosity, and further has a relatively high clear point (CP). When used in combination with the compounds represented by formula I and formula II, the liquid crystal mixture has low rotational viscosity and fast response speed.
本發明所提供的液晶組合物進一步可包含一種或多種式IV所示化合物
所述一種或多種式IV所示化合物較佳為IV0至IV25化合物
其中,X1、X2各自獨立地表示H或F; R7各自獨立地表示碳原子數為1-10的烷基、氟取代的碳原子數為1-10的烷基、碳原子數為1-10的烷氧基、氟取代的碳原子數為1-10的烷氧基、碳原子數為2-10的鏈烯基、氟取代的碳原子數為2-10的鏈烯基、碳原子數為3-8的鏈烯氧基或氟取代的碳原子數為3-8的鏈烯氧基,且該R7所示基團中任意一個或多個CH2可以被環戊基、環丁基或環丙基替代;(F)各自獨立地表示H或F。 Wherein, X 1 and X 2 each independently represent H or F; R 7 each independently represents an alkyl group with 1-10 carbon atoms, a fluorine-substituted alkyl group with 1-10 carbon atoms, and a carbon number of 1-10 alkoxy, fluorine-substituted alkoxy with 1-10 carbon atoms, alkenyl with 2-10 carbon atoms, fluorine-substituted alkenyl with 2-10 carbon atoms, carbon atoms, substituted carbon atoms, an alkenyloxy group or a 3-8-fluoro-3-8 alkenyloxy group, and the group represented by R7 is any one or more CH 2 groups may be cyclopentyl, Cyclobutyl or cyclopropyl substitution; (F) each independently represents H or F.
式IV所示化合物具有較大的介電各向異性(△ε),適當量添加有利於提升混合液晶的介電各向異性(△ε),降低液晶的驅動電壓。適用於正性TN、IPS、FFS模式使用,也可以適用PSA-正性TN、IPS、FFS模式使用。 The compound represented by formula IV has a large dielectric anisotropy (Δε), and the addition of an appropriate amount is beneficial to increase the dielectric anisotropy (Δε) of the mixed liquid crystal and reduce the driving voltage of the liquid crystal. It is suitable for use in positive TN, IPS, and FFS modes, and can also be used in PSA-positive TN, IPS, and FFS modes.
式IV所示化合物添加量較佳為在0-60%之間,更佳為5-30%。 The addition amount of the compound represented by formula IV is preferably between 0-60%, more preferably 5-30%.
所述液晶組合物進一步可包含一種或多種式V所示的化合物
所述一種或多種式V所示的化合物較佳為V1至V11化合物
所述液晶組合物進一步包含一種或多種式VI所示的化合物
所述的液晶組合物進一步可包含一種或多種式VII所示化合物
本發明包含上述液晶組合物的液晶顯示元件為主動矩陣顯示元件或被動矩陣顯示元件。 The liquid crystal display element of the present invention comprising the above-mentioned liquid crystal composition is an active matrix display element or a passive matrix display element.
顯示元件可以是TN、ECB、VA、IPS、FFS、PS-TN、PS-VA、PS-IPS、PS-FFS、PA-VA、PA-IPS、PA-FFS、PI-less VA、PI-less IPS、PI-less-FFS LCD模式。 Display elements can be TN, ECB, VA, IPS, FFS, PS-TN, PS-VA, PS-IPS, PS-FFS, PA-VA, PA-IPS, PA-FFS, PI-less VA, PI-less IPS, PI-less-FFS LCD mode.
下面結合具體實施例對本發明作進一步闡述,但本發明並不限於以下實施例。所述方法如無特別說明均為常規方法。所述原材料如無特別說明均能從公開商業途徑而得。 The present invention will be further described below in conjunction with specific embodiments, but the present invention is not limited to the following embodiments. The methods are conventional methods unless otherwise specified. The raw materials can be obtained from open commercial sources unless otherwise specified.
反應過程一般藉由TIC監控反應的進程,反應結束的後處理一般是水洗、提取、合併有機相後乾燥、減壓下蒸除溶劑,以及重結晶、柱層析,所屬技術領域中具有通常知識者都能夠按照下面的描述來實現本發明。 The reaction process is generally monitored by TIC, and the post-processing of the reaction is generally water washing, extraction, drying after merging the organic phases, evaporation of the solvent under reduced pressure, recrystallization, and column chromatography. Either can implement the present invention according to the following description.
本說明書中的百分比為質量百分比,溫度為攝氏度(℃),其他符號的具體意義及測試條件如下:Cp表示液晶清晰點(℃),DSC定量法測試;△n表示光學各向異性,no為尋常光的折射率,ne為非尋常光的折射率,測試條件為25±2℃,589nm,阿貝折射儀測試;△ε表示介電各向異性,△ε=ε∥-ε⊥,其中,ε∥為平行於分子軸的介電常數,ε⊥為垂直於分子軸的介電常數,測試條件為25數,測試℃,20微米平行盒,INSTEC:ALCT-IR1測試;γ1表示旋轉黏度(mPa.s),測試條件為25±0.5℃,20微米平行盒,INSTEC:ALCT-IR1測試;Tr(%)表示透射率,Tr(%)=100%*亮態(Vop)亮度/光源亮度,測試設備DMS501,測試條件為25±0.5℃,測試盒為3.3微米IPS測試盒,電極間距和電極寬度均為10微米,摩擦方向與電極夾角為10°,因ε⊥與Tr存在正相關性,所以考察透射率時,可用ε⊥作為考察指標來指證。 The percentages in this specification are mass percentages, and the temperature is in degrees Celsius (°C). The specific meanings and test conditions of other symbols are as follows: Cp represents the clear point of liquid crystal (°C), measured by DSC quantitative method; △n represents optical anisotropy, n o ordinary light refractive index, n e of the extraordinary light refractive index of the non-test conditions of 25 ± 2 ℃, 589nm, Abbe refractometer test; △ ε represents dielectric anisotropy, △ ε = ε ∥ -ε ⊥ , where ε ∥ is the dielectric constant parallel to the molecular axis, ε ⊥ is the dielectric constant perpendicular to the molecular axis, the test condition is 25 numbers, test ℃, 20 micron parallel box, INSTEC: ALCT-IR1 test; γ1 represents Rotational viscosity (mPa.s), test condition is 25±0.5℃, 20 micron parallel box, INSTEC: ALCT-IR1 test; Tr(%) means transmittance, Tr(%)=100%*brightness (Vop) brightness /Light source brightness, test equipment DMS501, test condition is 25±0.5℃, test box is 3.3 micron IPS test box, electrode spacing and electrode width are both 10 microns, friction direction and electrode angle are 10°, due to the existence of ε ⊥ and Tr There is a positive correlation, so when examining the transmittance, ε ⊥ can be used as an inspection index to prove it.
本文中所使用的「顯示元件」一詞,其涵蓋的範圍可包含一般所稱之顯示器、顯示裝置等。 As used herein, the term "display element" can cover what is generally called a display device, a display device, and the like.
本發明申請實施例液晶單體結構用代碼表示,液晶環結構、端基、連接基團的代碼表示方法見下表(一)、表(二) The structures of the liquid crystal monomers in the application examples of the present invention are represented by codes, and the code representation methods of the liquid crystal ring structures, end groups and connecting groups are shown in the following tables (1) and (2)
舉例:
比較例1:
比較例2:
實施例1:
將液晶組合物灌入測試盒進行測試得到:比較例1的透射率為5.4%,比較例2的透射率為5.3%,實施例1的透射率為6%,較比較例1、比較例2分別提高了11%和13%。 The liquid crystal composition was poured into the test box and tested to obtain: the transmittance of Comparative Example 1 was 5.4%, the transmittance of Comparative Example 2 was 5.3%, and the transmittance of Example 1 was 6%, compared with Comparative Example 1 and Comparative Example 2 That's an 11% and 13% increase, respectively.
實施例2:
實施例3:
實施例4:
實施例5:
實施例6:
實施例7:
實施例8:
實施例9:
實施例10:
實施例11:
實施例12:
本發明液晶組合物具有良好的對光和熱的穩定性,較低的黏 度,可以調節得到較為寬泛的折射率、較高的清晰點(很寬的使用溫度範圍),尤其是具有較高的光的穿透率,因而顯示元件具有較高的亮度或是具有節能省電的效果。 The liquid crystal composition of the present invention has good stability to light and heat, low viscosity It can be adjusted to obtain a wider refractive index, a higher clear point (a wide range of operating temperature), and especially a higher light transmittance, so the display element has higher brightness or energy saving. effect of electricity.
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Patent Citations (2)
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TW200932722A (en) * | 2007-11-30 | 2009-08-01 | Merck Patent Gmbh | Polymerisable compounds |
TW201710474A (en) * | 2015-09-02 | 2017-03-16 | 石家莊誠志永華顯示材料有限公司 | Liquid crystal compound with 2-fluorophenyl group and difluoro methyleneoxy group and preparing method and application thereof |
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TW201915147A (en) | 2019-04-16 |
US10655062B2 (en) | 2020-05-19 |
US20190100696A1 (en) | 2019-04-04 |
CN107603641B (en) | 2023-03-31 |
CN107603641A (en) | 2018-01-19 |
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